CN113527317A - Electroluminescent material and device - Google Patents
Electroluminescent material and device Download PDFInfo
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- CN113527317A CN113527317A CN202010285026.0A CN202010285026A CN113527317A CN 113527317 A CN113527317 A CN 113527317A CN 202010285026 A CN202010285026 A CN 202010285026A CN 113527317 A CN113527317 A CN 113527317A
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- 239000000463 material Substances 0.000 title claims abstract description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 238000009472 formulation Methods 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 306
- 125000001424 substituent group Chemical group 0.000 claims description 124
- -1 phosphino groups Chemical group 0.000 claims description 93
- 239000010410 layer Substances 0.000 claims description 69
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 41
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 37
- 229910052805 deuterium Inorganic materials 0.000 claims description 37
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000004104 aryloxy group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 18
- 125000005104 aryl silyl group Chemical group 0.000 claims description 18
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 238000006467 substitution reaction Methods 0.000 claims description 18
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
- 239000003446 ligand Substances 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 15
- 125000004185 ester group Chemical group 0.000 claims description 15
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 15
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 150000004696 coordination complex Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229940125904 compound 1 Drugs 0.000 claims description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000005580 triphenylene group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000006836 terphenylene group Chemical group 0.000 claims description 2
- 125000005730 thiophenylene group Chemical group 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 abstract description 11
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract description 10
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 abstract description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000003111 delayed effect Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 150000003384 small molecules Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical class C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000477 aza group Chemical group 0.000 description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229920001621 AMOLED Polymers 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical group C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000005669 field effect Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000006504 o-cyanobenzyl group Chemical group [H]C1=C([H])C(C#N)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000013086 organic photovoltaic Methods 0.000 description 2
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical group C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003246 quinazolines Chemical class 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- HWIATMHDQVGMFQ-UHFFFAOYSA-N 1,3-azaborinine Chemical compound B1=CC=CN=C1 HWIATMHDQVGMFQ-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- OBUDOIAYABJUHQ-UHFFFAOYSA-N 1,4-azaborinine Chemical compound B1=CC=NC=C1 OBUDOIAYABJUHQ-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical compound C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- IEBQZJXMAOMNBO-UHFFFAOYSA-N 1h-indole;pyridine Chemical compound C1=CC=NC=C1.C1=CC=C2NC=CC2=C1 IEBQZJXMAOMNBO-UHFFFAOYSA-N 0.000 description 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
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- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- QZLAKPGRUFFNRD-UHFFFAOYSA-N [1]benzoselenolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3[se]C2=C1 QZLAKPGRUFFNRD-UHFFFAOYSA-N 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- KCQLSIKUOYWBAO-UHFFFAOYSA-N azaborinine Chemical compound B1=NC=CC=C1 KCQLSIKUOYWBAO-UHFFFAOYSA-N 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
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- 238000012512 characterization method Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
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- 239000011259 mixed solution Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000002829 nitrogen Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical compound O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Chemical group C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- XDJOIMJURHQYDW-UHFFFAOYSA-N phenalene Chemical group C1=CC(CC=C2)=C3C2=CC=CC3=C1 XDJOIMJURHQYDW-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
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- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/16—Peri-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
Abstract
An electroluminescent material and device are disclosed. The electroluminescent material is a compound formed by bonding indole and pyrrole fused azamacrocycles, quinazoline and similar structures thereof at specific positions, and can be used as a main body material in an electroluminescent device. The novel compounds can effectively improve the efficiency of the device and can provide better device performance. An electroluminescent device and compound formulation are also disclosed.
Description
Technical Field
The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a compound in which indole and pyrrole fused azamacrocycles are bonded with quinazoline and the like at specific positions, and an organic electroluminescent device and a compound formulation comprising the same.
Background
Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.
In 1987, Tang and Van Slyke of Islamic Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987,51(12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are a self-emissive solid state device, it offers great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in the fabrication of flexible substrates.
OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of active matrix OLEDs (amoleds). Recently, Adachi has achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
OLEDs can also be classified into small molecule and polymer OLEDs depending on the form of the material used. Small molecule refers to any organic or organometallic material that is not a polymer. The molecular weight of small molecules can be large, as long as they have a precise structure. Dendrimers with well-defined structures are considered small molecules. The polymeric OLED comprises a conjugated polymer and a non-conjugated polymer having a pendant light-emitting group. Small molecule OLEDs can become polymer OLEDs if post-polymerization occurs during the fabrication process.
Various OLED manufacturing methods exist. Small molecule OLEDs are typically fabricated by vacuum thermal evaporation. Polymer OLEDs are fabricated by solution processes such as spin coating, ink jet printing and nozzle printing. Small molecule OLEDs can also be made by solution processes if the material can be dissolved or dispersed in a solvent.
The light emitting color of the OLED can be realized by the structural design of the light emitting material. An OLED may comprise one light emitting layer or a plurality of light emitting layers to achieve a desired spectrum. Green, yellow and red OLEDs, phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still have the problems of blue unsaturation, short device lifetime, high operating voltage, and the like. Commercial full-color OLED displays typically employ a hybrid strategy, using either blue fluorescence and phosphorescent yellow, or red and green. At present, the rapid decrease in efficiency of phosphorescent OLEDs at high luminance is still a problem. In addition, it is desirable to have a more saturated emission spectrum, higher efficiency and longer device lifetime.
For the development of phosphorescent OLEDs, it is an important and extensive research direction to design and synthesize suitable host materials for use with phosphorescent light-emitting materials.
In US20180337340A1 is disclosed having
A compound of the general structure wherein X and Y each independently represent CR4Or N, specific examples being
Obviously, the inventor of the application pays attention to the compound obtained by connecting quinazoline structural units by an aza-seven-membered ring fused ring structure as a phosphorescent hostThe advantages of the materials, but it does not disclose or teach the use of an aza seven-membered ring fused ring structure in conjunction with a specific position of a quinazoline and similar structures, such as the 4-position of the quinazoline.
Many host materials with different structures have been developed, but the related device properties such as device efficiency, driving voltage, lifetime, etc. have still disadvantages, and further research and development are still in need.
Disclosure of Invention
The present invention aims to solve at least some of the above problems by providing a series of compounds having indole and pyrrole fused azamacrocycle linked quinazolines and similar structures. The compounds are useful as host materials in organic electroluminescent devices. The novel compounds can effectively improve the efficiency of the device and can provide better device performance.
According to one embodiment of the invention, a compound is disclosed having the structure of H-L-E,
wherein H has a structure represented by formula 1:
wherein, in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rxrepresents mono-, poly-or unsubstituted;
wherein E has a structure represented by formula 2:
wherein, in formula 2, Y1To Y7Selected, identically or differently, on each occurrence from N or CRyAnd, Y5To Y7Any two of which are selected from N and the other from CRy；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
wherein R, RXAnd RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents R, RXCan optionally be linked to form a ring;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising an anode, a cathode, an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having the structure of H-L-E as described in the above embodiment.
According to another embodiment of the invention, a compound formulation is also disclosed, comprising the compound having the structure of H-L-E.
According to another embodiment of the present invention, a display assembly is also disclosed, which comprises the electroluminescent device described in the above embodiment.
The novel compounds having indole and pyrrole fused azamacrocycle linked quinazolines and their analogous structures disclosed herein are useful as host materials in electroluminescent devices. The novel compounds can effectively improve the efficiency of the device and can provide better device performance.
Drawings
FIG. 1 is a schematic representation of an organic light emitting device that can contain the compounds and compound formulations disclosed herein.
Fig. 2 is a schematic view of another organic light emitting device that can contain compounds and compound formulations disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the layers, as well as exemplary materials, are described in more detail in U.S. patent US7,279,704B2, columns 6-10, which is incorporated herein by reference in its entirety.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:14TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose the use of cathodesExamples include composite cathodes having a thin layer of a metal such as Mg: Ag with an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
The above-described hierarchical structure is provided via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.
The materials and structures described herein may also be used in other organic electronic devices as previously listed.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as being "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).
On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small mono-triplet gap in order to switch between energy states. Thermal energy can activate the transition from the triplet state back to the singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. If the reverse intersystem crossing (RISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of backfill singlet excited states may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.
The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε)S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ ES-T. These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).
Definitions for substituent terms
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-comprises both straight and branched chain alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. The carbons in the alkyl chain may be substituted with other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferable.
Cycloalkyl-as used herein, comprises a cyclic alkyl group. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms and include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. In addition, the cycloalkyl group may be optionally substituted. The carbon in the ring may be substituted with other heteroatoms.
Alkenyl-as used herein, encompasses both straight and branched chain olefinic groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-methylallyl group, a 1-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group and a 3-phenyl-1-butenyl group. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight and branched alkynyl groups are contemplated. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. Preferred aryl groups are those containing from 6 to 60 carbon atoms, more preferably from 6 to 20 carbon atoms, and even more preferably from 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene,
perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, s-trixylylTolyl and m-tetrabiphenyl groups.
Heterocyclyl or heterocyclic-as used herein, aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclic group may also be an aromatic heterocyclic group having at least one hetero atom selected from a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups are contemplated which may contain 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing from 3 to 30 carbon atoms, more preferably from 3 to 20 carbon atoms, more preferably from 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indoline, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuropyridine, furobipyridine, benzothienopyridine, thienobipyridine, cinnolino, benzoselenophenopyridine, selenobenzene, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, borazole, and aza analogues thereof. In addition, the heteroaryl group may be optionally substituted.
Alkoxy-is represented by-O-alkyl. Examples and preferred examples of the alkyl group are the same as those described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy. The alkoxy group having 3 or more carbon atoms may be linear, cyclic or branched.
Aryloxy-is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. Examples of the aryloxy group having 6 to 40 carbon atoms include a phenoxy group and a biphenyloxy group.
Aralkyl-as used herein, an alkyl group having an aryl substituent. In addition, the aralkyl group may be optionally substituted. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable.
The term "aza" in aza-dibenzofuran, aza-dibenzothiophene, etc., means that one or more C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.
In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amine, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, meaning alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amine, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which groups may be substituted with one or more moieties selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, unsubstituted aralkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted alkylsilyl having 3 to 20 carbon atoms, unsubstituted arylsilyl having 6 to 20 carbon atoms, unsubstituted amine group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof.
It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered to be equivalent.
In the compounds mentioned in the present disclosure, a hydrogen atom may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.
In the compounds mentioned in the present disclosure, multiple substitution means that a double substitution is included up to the range of the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.
In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as substituents bonded to carbon atoms directly bonded to each other.
The expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
the expression that adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
further, the expression that adjacent substituents can be optionally connected to form a ring is also intended to be taken to mean that, in the case where one of two substituents bonded to carbon atoms directly bonded to each other represents hydrogen, the second substituent is bonded at a position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:
according to one embodiment of the invention, a compound is disclosed having the structure of H-L-E,
wherein H has a structure represented by formula 1:
wherein, in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rxthe same or different at each occurrence denotes mono-, poly-or no-substitution;
wherein E has a structure represented by formula 2:
wherein, in formula 2, Y1To Y7Selected, identically or differently, on each occurrence from N or CRyAnd, Y5To Y7Any two of which are selected from N and the other from CRy；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
wherein R, RXAnd RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents R, RXCan optionally be linked to form a ring;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
In the present embodiment, "+" in formula 1 denotes a position where the structure represented by formula 1 is connected to L; "") in formula 2 represents a position where the structure represented by formula 2 is connected to the L.
In this context, the adjacent substituents R, RXCan optionally be linked to form a ring, intended to mean between adjacent substituents, e.g. between two R, two RXR and RXOptionally linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
In this context, adjacent substituents RyCan optionally be linked to form a ring, intended to mean any two adjacent RyCan be connected to form a ring. Obviously, adjacent RyMay not be connected to form a ring.
According to one embodiment of the present invention, wherein, in formula 1, the ring a, the ring B and the ring C, which occur identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, an aromatic ring having 6 to 18 carbon atoms, or a heteroaromatic ring having 3 to 18 carbon atoms.
According to one embodiment of the present invention, wherein, in formula 1, the ring A, the ring B and the ring C, which may be the same or different at each occurrence, are selected from a 5-membered carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring having 3 to 4 carbon atoms, or a 6-membered heteroaromatic ring having 3 to 5 carbon atoms
According to an embodiment of the present invention, wherein the H has a structure represented by formula 1-a:
wherein A is1To A3Selected, identically or differently, on each occurrence from N or CR, X1To X10Selected, identically or differently, on each occurrence from N or CRx；
Wherein R, RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents R, RxCan optionally be linked to form a ring.
In this example, the adjacent substituents R, RxCan optionally be linked to form a ring, is intended to mean that adjacent substituents R can optionally be linked to form a ring, is also intended to mean X1To X3In (B) an adjacent substituent RxCan optionally be linked to form a ring, is also intended to denote X4To X6In (B) an adjacent substituent RxCan optionally be linked to form a ring, is also intended to denote X7To X10In (B) an adjacent substituent RxCan optionally be linked to form a ring, and are also intended to represent adjacent substituents RXR and RxCan optionally be joined to form a ring, e.g. A1And X3And/or A3And X10And/or X6And X7Can be optionally connected into a ring; it is obvious to the person skilled in the art that the adjacent substituents R, RxOr may not be linked to form a ring, in which case adjacent substituents R are not linked to form a ring, and/or adjacent substituents RxNor linked to form a ring, and/or adjacent substituents R and RxNor are they linked to form a ring.
According to one embodiment of the invention, wherein R, RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having from 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having from 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having from 2 to 20 carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted amine having from 0 to 20 carbon atoms, cyano, isocyano, mercapto, and combinations thereof;
wherein the adjacent substituents R, RxCan optionally be linked to form a ring.
In this example, the adjacent substituents R, RxCan optionally be linked to form a ring, it is intended to mean that adjacent substituents R can optionally be linked to form a ring, alsoIs intended to represent X1To X3In (B) an adjacent substituent RxCan optionally be linked to form a ring, is also intended to denote X4To X6In (B) an adjacent substituent RxCan optionally be linked to form a ring, is also intended to denote X7To X10In (B) an adjacent substituent RxCan optionally be linked to form a ring, and are also intended to represent adjacent substituents RXR and RxCan optionally be joined to form a ring, e.g. A1And X3And/or A3And X10And/or X6And X7Can be optionally connected into a ring; it is obvious to the person skilled in the art that the adjacent substituents R, RxOr may not be linked to form a ring, in which case adjacent substituents R are not linked to form a ring, and/or adjacent substituents RxNor linked to form a ring, and/or adjacent substituents R and RxNor are they linked to form a ring.
According to one embodiment of the present invention, wherein in said formula 1-a, R and RxAt least one of which is selected from deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.
According to one embodiment of the present invention, wherein in said formula 1-a, R and RxAt least one of which is selected from deuterium, phenyl, biphenyl, or pyridyl.
According to an embodiment of the present invention, wherein in said formula 1-a, A1To A3Adjacent substituents R, X between1To X3Adjacent substituent R betweenx，X4To X6Adjacent substituent R betweenxAnd X7To X10Adjacent substituent R betweenxAt least one of these adjacent substituent groups is linked to form a ring.
In this embodiment, at least one of the adjacent substituent groups is linked to form a ring, which is intended to mean that for the adjacent substituent groups present in formula 1-a, for example, A1And A2Two adjacent substituents R, A2And A3Two inAdjacent substituents R, X1And X2Two adjacent substituents R inx，X2And X3Two adjacent substituents R inx，X4And X5Two adjacent substituents R inx，X5And X6Two adjacent substituents R inx，X7And X8Two adjacent substituents R inx，X8And X9Two adjacent substituents R inxAnd X9And X10Two adjacent substituents R inxAt least one of these substituent groups is linked to form a ring.
According to one embodiment of the invention, wherein H is selected from the group consisting of the following structures:
according to one embodiment of the present invention, wherein, optionally, the hydrogen in the above structures of H-1 to H-130 can be partially or completely substituted with deuterium.
According to an embodiment of the present invention, wherein the E has a structure represented by formula 2-a or formula 2-b:
wherein Y is selected from CR, the same or different at each occurrencey；
Wherein R isyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; and at least one R is presentyAnd said R isyIs not hydrogen;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
According to one embodiment of the invention, wherein E is selected from the group consisting of:
wherein R isyThe same or different at each occurrence denotes mono-, poly-or no-substitution;
Ryeach occurrence ofThe same or different at times is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having from 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having from 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having from 2 to 20 carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted amine having from 0 to 20 carbon atoms, cyano, isocyano, mercapto, and combinations thereof.
According to one embodiment of the invention, wherein E is selected from the group consisting of:
wherein R isyThe same or different at each occurrence denotes mono-, poly-or no-substitution;
Ryeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano, and combinations thereof.
According to one embodiment of the invention, wherein E is selected from the group consisting of:
wherein R isyThe same or different at each occurrence denotes mono-, poly-or no-substitution;
Ryeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, phenyl, biphenyl, naphthyl, terphenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, 9, 9-dimethylsilylfluorenyl, 9, 9-dimethylfluorenyl, carbazolyl, pyridyl, 4-cyanophenyl, azacarbazylAzolyl, azabicyclofuranyl, azabicyclothiophene, triphenylene, and combinations thereof.
According to one embodiment of the present invention, wherein in the structure represented by formula 2-a or formula 2-b, Y in the aza six-membered ring is selected from CRyAnd said R isySelected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
According to one embodiment of the present invention, wherein in the structure represented by formula 2-a or formula 2-b, Y in the aza six-membered ring is selected from CRyAnd said R isySelected from phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, dimethylsilfluorenyl, azabicyclobenzofuranyl, azabicycloheptanophenyl, azacarbazolyl, carbazolylalkylnaphthyl or pyridyl.
According to one embodiment of the invention, wherein E is selected from the group consisting of:
according to one embodiment of the present invention, wherein hydrogen in the above structures of E-1 to E-191 can be partially or completely substituted with deuterium.
According to an embodiment of the invention, wherein L is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzofuranylene, dibenzothiophenene, pyridinylene, thiophenylene, and combinations thereof.
According to an embodiment of the invention, wherein L is selected from the group consisting of:
according to one embodiment of the present invention, wherein, optionally, the hydrogen in the structures of L-1 to L-26 above can be partially or completely substituted with deuterium.
According to an embodiment of the invention, wherein the compound having the structure of H-L-E is selected from the group consisting of compound 1 to compound 879. The specific structures of said compound 1 to compound 879 are found in claim 13.
According to an embodiment of the invention, wherein hydrogen in said compounds 1 to 879 can be partially or completely substituted by deuterium.
According to an embodiment of the present invention, there is also disclosed an electroluminescent device, including:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having a structure of H-L-E,
wherein H has a structure represented by formula 1:
wherein, in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rxrepresents mono-, poly-or unsubstituted;
wherein E has a structure represented by formula 2:
wherein, in formula 2, Y1To Y7Selected, identically or differently, on each occurrence from N or CRyAnd, Y5To Y7Any two of which are selected from N and the other from CRy；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
wherein R, RXAnd RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted aralkyl, substituted aralkyl, or substituted aralkyl, or substituted aralkyl, or substituted aralkyl, or unsubstituted aralkyl, substituted aralkyl, or unsubstituted aralkyl, or substituted aralkyl, or unsubstituted aralkyl, or substituted aralkyl, or substituted aralkyl, or substituted aralkylOr unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amine having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein the adjacent substituents R, RXCan optionally be linked to form a ring;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
According to one embodiment of the present invention, in the device, the organic layer is a light emitting layer, and the compound is a host material.
According to one embodiment of the invention, in the device, the light emitting layer further comprises at least one phosphorescent light emitting material.
According to one embodiment of the invention, in the device, the phosphorescent light emitting material is a metal complex comprising at least one ligand comprising the structure of any one of:
wherein the content of the first and second substances,
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or unsubstituted;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1And CRC1RC2；
XcAnd XdEach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
in the ligand structure, adjacent substituents can optionally be linked to form a ring.
In this example, adjacent substituents can optionally be joined to form a ring, intended to mean wherein adjacent groups of substituents, for example, two substituents RaIn between, two substituents RbIn between, two substituents RcOf a substituent RaAnd RbOf a substituent RaAnd RcOf a substituent RbAnd RcOf a substituent RaAnd RN1Of a substituent RbAnd RN1Of a substituent RaAnd RC1Of a substituent RaAnd RC2Of a substituent RbAnd RC1Of a substituent RbAnd RC2Of a substituent RaAnd RN2Of a substituent RbAnd RN2And R isC1And RC2Wherein any one or more of these substituent groups may be connectedLooping. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand having the following structure:
wherein R is1To R7Each independently selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
According to one embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand having the following structure:
wherein R is1-R3At least one selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted alkyl groups having 3 to 2 carbon atomsCycloalkyl of 0 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least one of which is selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand having the following structure:
wherein R is1-R3At least two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the present invention, in the device, wherein the phosphorescent light-emitting material is a metal complex, the metal complex comprises at least one ligand having the following structure:
wherein R is1-R3At least two of which are selected, identically or differently on each occurrence, from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted cycloalkyl groups having 2 to 20 carbon atoms, or a combination thereof; and/or R4-R6At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
According to an embodiment of the present invention, in the device, wherein the phosphorescent light emitting material is an Ir, Pt or Os complex.
According to an embodiment of the present invention, the device, wherein the phosphorescent light emitting material is an Ir complex and has Ir (L)a)(Lb)(Lc) The structure of (1);
wherein L isa，LbAnd LcEach occurrence, identically or differently, is selected from any one of the group consisting of:
wherein the content of the first and second substances,
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or unsubstituted;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1And CRC1RC2；
XcAnd XdEach occurrence, the same or different, is selected from the group consisting of: o, S, Se and NRN2；
Ra，Rb，Rc，RN1，RN2，RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms,substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
in the ligand structure, adjacent substituents can optionally be linked to form a ring.
In this example, adjacent substituents can optionally be joined to form a ring, intended to mean wherein adjacent groups of substituents, for example, two substituents RaIn between, two substituents RbIn between, two substituents RcOf a substituent RaAnd RbOf a substituent RaAnd RcOf a substituent RbAnd RcOf a substituent RaAnd RN1Of a substituent RbAnd RN1Of a substituent RaAnd RC1Of a substituent RaAnd RC2Of a substituent RbAnd RC1Of a substituent RbAnd RC2Of a substituent RaAnd RN2Of a substituent RbAnd RN2And R isC1And RC2And any one or more of these substituent groups may be linked to form a ring. Obviously, none of these substituents may be connected to each other to form a ring.
According to one embodiment of the present invention, the device, wherein the Ir complex is selected from the group consisting of:
wherein, XfEach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN3,CRC3RC4；
Wherein, XeSelected from CR, identically or differently at each occurrencedOr N;
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or no substitution;
Ra，Rb，Rc，Rd，RN3，RC3and RC4Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof.
According to another embodiment of the invention, a compound formulation is also disclosed that includes a compound having the structure of H-L-E. The specific structure of the compound is shown in any one of the embodiments.
According to another embodiment of the present invention, there is also disclosed a display assembly comprising the electroluminescent device of any of the above embodiments.
In combination with other materials
The materials described herein for use in particular layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application Ser. No. 0132-0161 of U.S. 2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein may be used in conjunction with a variety of hosts, light emitting dopants, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. US2015/0349273A1, paragraph 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai prism-based fluorescence spectrophotometer, Wuhan Corset's electrochemical workstation, Anhui Beidek's sublimator, etc.) in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, Suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.
Materials synthesis example:
the preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limited to, and the synthetic route and the preparation method thereof are as follows:
synthesis example 1: synthesis of Compound 1
Step 1: synthesis of intermediate 1
2-bromo-3-chloronitrobenzene (100g, 425.5mmol), 2-aminophenylboronic acid pinacol ester (102g, 468.1mmol), tetratriphenylphosphine palladium (4.9g, 4.25mmol), potassium carbonate (115g, 852mmol), toluene (1000mL), water (200mL) and ethanol (200mL) were added to a three-necked flask under nitrogen and reacted at 100 ℃ for 48 h. After completion of the reaction, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and column chromatography purification (PE/EA ═ 4:1) gave intermediate 1(90g, yield: 85%) as a yellow oil.
Step 2: synthesis of intermediate 2
Intermediate 1(90g, 363mmol) and acetonitrile (1000mL) were each placed in a three-necked flask, p-toluenesulfonic acid (193.2g, 1088mmol) was added portionwise at 0 ℃ and stirred for 30min, at which temperature an aqueous solution of a mixture of sodium nitrite (69g, 726mmol) and potassium iodide (150.6g, 907mmol) was slowly added dropwise. After the dropwise addition, the temperature was slowly raised to room temperature, and the reaction was carried out for 12 hours. After completion of the reaction, the reaction was quenched by dropwise addition of an aqueous solution of saturated sodium thiosulfate, the reaction solution was concentrated and diluted with water, the mixed solution was extracted three times with ethyl acetate, the organic phase was dried over anhydrous sodium sulfate and concentrated to remove the solvent, and the mixture was subjected to column chromatography (PE/DCM ═ 10/1) to give intermediate 2(85g, yield: 65%) as a yellow solid.
And step 3: synthesis of intermediate 4
Intermediate 2(20g, 55.7mmol), intermediate 3(24.5g, 83.6mmol), tetrakistriphenylphosphine palladium (1.9g, 1.67mmol), potassium carbonate (15.4g, 111.4mmol), tetrahydrofuran (500mL), water (100mL), ethanol (100mL) were added to a three-necked flask under nitrogen and reacted at 70 ℃ for 48 h. After completion of the reaction, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and purified by column chromatography (PE/EA ═ 4:1) to obtain intermediate 4(12g, yield: 55%) as a yellow solid.
And 4, step 4: synthesis of intermediate 5
Intermediate 4(12g, 30.15mmol), palladium acetate (338mg, 1.5mmol), tri-tert-butylphosphine (606mg, 3.0mmol), cesium carbonate (20g, 60.3mmol) and xylene (230mL) were added to a three-necked flask under nitrogen and reacted at 140 ℃ for 10 h. After completion of the reaction, it was cooled to room temperature, concentrated to remove the solvent, distilled water was added, the mixture was extracted with ethyl acetate, the organic phase was washed with water, the organic phase was dried over anhydrous magnesium sulfate and concentrated to remove the solvent, and column chromatography purification (PE/EA ═ 6:1) gave intermediate 5(9g, yield: 80%) as a yellow solid.
And 5: synthesis of intermediate 6
Intermediate 5(9g, 24.9mmol), triphenylphosphine (19.6g, 74.7mmol) and o-dichlorobenzene (o-DCB) (100mL) were added to a three-necked flask under nitrogen and reacted at 200 ℃ for 12 h. After completion of the reaction, the solvent was removed by concentration, and the crude product was separated by column chromatography to give intermediate 6(7g, yield: 85%) as a yellow solid.
Step 6: synthesis of Compound 1
Intermediate 7(2.4g, 10mmol), intermediate 6(3g, 9.1mmol), palladium acetate (101.9mg, 0.46mmol), cesium carbonate (5.9g, 18.2mmol), 2-dicyclohexylphosphine-2 ', 6 ' -dimethoxy-1, 1 ' -biphenyl (Sphos) (373mg, 0.9mmol) and xylene (100mL) were added to a three-necked flask under nitrogen and refluxed overnight. After cooling to room temperature, water was added to precipitate a solid, which was filtered off and recrystallized from toluene to obtain Compound 1(4.5g, yield: 94%) as a yellow solid, which was confirmed to be the objective product having a molecular weight of 534.2.
It will be appreciated by those skilled in the art that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other structures of the compounds of the present invention.
Device embodiments
Device example 1
First, a glass substrate, having an Indium Tin Oxide (ITO) anode 120nm thick, was cleaned and then treated with UV ozone and oxygen plasma. After the treatment, the substrate was dried in a glove box filled with nitrogen gas to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees-8In the case of Torr
Is passed through heatAnd carrying out vacuum evaporation on the ITO anode in sequence. Compound HI was used as a Hole Injection Layer (HIL) with a thickness of
The compound HT is used as Hole Transport Layer (HTL) with a thickness of
Compound EB was used as an Electron Blocking Layer (EBL) with a thickness of
Then, the compound 1 of the present invention as a host and the compound RD as a dopant were co-evaporated to be used as an emission layer (EML) with a thickness of
The compound HB was used as a hole-blocking layer (HBL) with a thickness of
On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an electron-transporting layer (ETL) with a thickness of
Finally, evaporation
8-hydroxyquinoline-lithium (Liq) as an Electron Injection Layer (EIL) in thickness and evaporation deposited
As a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.
Device comparative example 1
Device comparative example 1 was the same as device example 1 except that compound a was used as a host in place of compound 1 of the present invention in the light emitting layer (EML).
The detailed device layer structure and thickness are shown in the table below. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
TABLE 1 device structures of device examples and comparative examples
The material structure used in the device is as follows:
table 2 shows the values at 15mA/cm2Current Efficiency (CE), maximum wavelength (lambda) measured under the conditionsmax) And External Quantum Efficiency (EQE).
TABLE 2 device data
Discussion:
as shown in Table 2, at 15mA/cm2The EQE of the example 1 measured under the current density is 24.9 percent, which is 6.1 percent higher than the EQE (18.8 percent) of the comparative example 1, and the promotion amplitude reaches 32 percent; CE (20) of example 1 was improved by 33% as compared with CE (15) of comparative example 1; the maximum wavelengths of example 1 and comparative example 1 remained substantially the same; the data show that the examples have more excellent device properties, that is, the compound of the present invention having a hole transport unit formed by an indole and pyrrole fused azamacrocycle and bonded to a specific position (4-position) of an electron transport unit of quinazoline and the like, has better electron transport stability due to the change in the position of bonding of the electron transport unit than the comparative compound a bonded to the 2-position of quinazoline as the electron transport unit, and can make the hole transport in the light emitting layer more stableThe electron transmission and electron transmission reach a more balanced state, so that the luminous efficiency of the device is greatly improved, and the performance of the device is remarkably improved. The unusual advantages of the compounds of the present invention are demonstrated.
It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Thus, the invention as claimed may include variations from the specific embodiments and preferred embodiments described herein, as will be apparent to those skilled in the art. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that various theories as to why the invention works are not intended to be limiting.
Claims (21)
1. A compound having the structure H-L-E,
wherein H has a structure represented by formula 1:
wherein, in formula 1, A1、A2And A3Each occurrence is selected, identically or differently, from N or CR, and each occurrence of ring A, ring B and ring C is selected, identically or differently, from a carbocyclic ring having from 5 to 18 carbon atoms, or a heterocyclic ring having from 3 to 18 carbon atoms;
Rxthe same or different at each occurrence denotes mono-, poly-or no-substitution;
wherein E has a structure represented by formula 2:
wherein, in formula 2, Y1To Y7Selected, identically or differently, on each occurrence from N or CRyAnd, Y5To Y7Any two of which are selected from N and the other from CRy；
L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;
wherein R, RXAnd RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents R, RXCan optionally be linked to form a ring;
wherein the adjacent substituents RyCan optionally be linked to form a ring.
2. The compound of claim 1, wherein each occurrence of ring a, ring B, and ring C, the same or different, is selected from a 5-membered carbocyclic ring, an aromatic ring having 6-18 carbon atoms, or a heteroaromatic ring having 3-18 carbon atoms;
preferably, said ring a, ring B and ring C, identically or differently at each occurrence, are selected from a 5-membered carbocyclic ring, a benzene ring, a 5-membered heteroaromatic ring having 3 to 4 carbon atoms, or a 6-membered heteroaromatic ring having 3 to 5 carbon atoms.
3. The compound of claim 2, wherein the H has a structure represented by formula 1-a:
wherein A is1To A3Selected, identically or differently, on each occurrence from N or CR, X1To X10Selected, identically or differently, on each occurrence from N or CRx；
Wherein R, RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein the adjacent substituents R, RxCan optionally be linked to form a ring.
4. The compound of claim 3, wherein R, RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 6 to 30 carbon atomsAn aryl group of atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted amine group having 0 to 20 carbon atoms, a cyano group, an isocyano group, a mercapto group, and combinations thereof;
wherein the adjacent substituents R, RxCan optionally be linked to form a ring.
5. A compound according to claim 3 or 4, wherein R and RxAt least one of which is selected from deuterium, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms;
preferably, R and RxAt least one of which is selected from deuterium, phenyl, biphenyl, or pyridyl.
6. The compound of claim 3 or 4, wherein A is1To A3Adjacent substituents R, X between1To X3Adjacent substituent R betweenx，X4To X6Adjacent substituent R betweenxAnd X7To X10Adjacent substituent R betweenxAt least one of these adjacent substituent groups is linked to form a ring.
7. The compound of any one of claims 1 to 6, wherein said H is selected from the group consisting of the following structures:
wherein, optionally, the hydrogen in the above structure can be partially or fully substituted with deuterium.
8. The compound of any one of claims 1 to 7, wherein said E has a structure represented by formula 2-a or formula 2-b:
wherein Y is selected from CR, the same or different at each occurrencey；
Wherein R isyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof; and at least one R other than hydrogen is presenty；
Wherein are adjacent to each otherSubstituent R ofyCan optionally be linked to form a ring.
9. The compound of claim 8, wherein said E has a structure represented by any one selected from the group consisting of:
wherein R isyThe same or different at each occurrence denotes mono-, poly-or no-substitution;
Ryeach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted heteroalkyl having from 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having from 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having from 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having from 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having from 2 to 20 carbon atoms, substituted or unsubstituted aryl having from 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having from 3 to 30 carbon atoms, substituted or unsubstituted amine having from 0 to 20 carbon atoms, cyano, isocyano, mercapto, and combinations thereof;
preferably, RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, cyano, and combinations thereof;
more preferably, RyEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, phenyl, biphenyl, naphthyl, terphenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, 9, 9-dimethylsilylfluorenyl, 9, 9-dimethylfluorenyl, carbazolyl, pyridinyl, 4-cyanophenyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenyl, triphenylene, and combinations thereof.
10. The method of claim 8Wherein, in the structure represented by formula 2-a or formula 2-b, Y in the aza six-membered ring is selected from CRyAnd said R isySelected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms;
preferably, said R isySelected from phenyl, biphenyl, terphenyl, naphthyl, naphthylphenyl, dibenzofuranyl, dibenzothiophenyl, triphenylene, carbazolyl, 9-phenylcarbazolyl, 9, 9-dimethylfluorenyl, dimethylsilfluorenyl, azabicyclobenzofuranyl, azabicycloheptanophenyl, azacarbazolyl, carbazolylalkylnaphthyl or pyridyl.
11. The compound of claim 9 or 10, wherein E is selected from the group consisting of the following structures:
wherein, optionally, the hydrogen in the above structure can be partially or fully substituted with deuterium.
12. The compound of any one of claims 1 to 11, wherein L is selected from the group consisting of: a single bond, phenylene, naphthylene, biphenylene, terphenylene, triphenylene, dibenzofuranylene, dibenzothiophenene, pyridinylene, thiophenylene, and combinations thereof;
preferably, said L is selected from the group consisting of the following structures:
wherein, optionally, the hydrogen in the structures of L-1 to L-26 above can be partially or completely substituted with deuterium.
13. The compound of claim 12, wherein the compound is selected from the group consisting of compound 1 to compound 879, wherein the compound 1 to compound 879 have the structure of H-L-E, wherein H, L and E each correspond to a structure selected from the following table:
wherein, optionally, the hydrogen in the structure of the above compound can be partially or completely substituted with deuterium.
14. An electroluminescent device, comprising:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising the compound of any one of claims 1 to 13.
15. The electroluminescent device of claim 14, wherein the organic layer is a light emitting layer and the compound is a host material.
16. The electroluminescent device of claim 15 wherein said light-emitting layer further comprises at least one phosphorescent light-emitting material.
17. The electroluminescent device of claim 16, wherein the phosphorescent light-emitting material is a metal complex comprising at least one ligand comprising the structure of any one of:
wherein the content of the first and second substances,
Ra,Rband RcThe same or different at each occurrence represents mono-, poly-, or unsubstituted, and each may be the same or different at each occurrence;
Xbeach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN1,CRC1RC2；
XcAnd XdEach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN2；
Ra,Rb,Rc,RN1,RN2,RC1And RC2Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine groups having 0-20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
in the ligand structure, adjacent substituents can optionally be linked to form a ring.
18. The electroluminescent device of claim 16, wherein the phosphorescent light-emitting material is a metal complex comprising at least one ligand having the structure:
wherein R is1To R7Each independently selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstitutedSubstituted heteroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, substituted or unsubstituted amine group having 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, a phosphine group, and combinations thereof;
preferably, wherein R1-R3At least one or two of which are selected from the group consisting of substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least one or two of which are selected from substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, or combinations thereof;
more preferably, R1-R3At least two of which, identically or differently on each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof; and/or R4-R6At least two of which, identically or differently at each occurrence, are selected from substituted or unsubstituted alkyl groups having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 2 to 20 carbon atoms, or combinations thereof.
19. An electroluminescent device as claimed in claim 17 or 18 wherein the phosphorescent light emitting material is an Ir, Pt or Os complex;
preferably, wherein the phosphorescent light-emitting material is an Ir complex and has Ir (L)a)(Lb)(Lc) The structure of (1);
wherein L isa，LbAnd LcA ligand selected from any of the above, identically or differently at each occurrence;
more preferably, wherein said Ir complex is selected from the group consisting of the following structures:
wherein, XfEach occurrence, the same or different, is selected from the group consisting of: o, S, Se, NRN3,CRC3RC4；
Wherein, XeSelected from CR, identically or differently at each occurrencedOr N;
Ra，Rband RcThe same or different at each occurrence represents mono-, poly-, or no substitution;
Ra，Rb，Rc，Rd，RN3，RC3and RC4Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amine, acyl, carbonyl, carboxylic acid, ester, cyano, iso-amino having 0 to 20 carbon atomsCyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
20. A compound formulation comprising a compound of any one of claims 1 to 13.
21. A display assembly comprising an electroluminescent device as claimed in any one of claims 14 to 19.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114437086A (en) * | 2022-02-24 | 2022-05-06 | 阜阳欣奕华材料科技有限公司 | Dicarbazole compound and preparation method and application thereof |
| CN115819427A (en) * | 2023-02-23 | 2023-03-21 | 夏禾科技(江苏)有限公司 | Synthetic method of benzo-quinoxaline-substituted indole and pyrrole fused azamacrocyclic compound |
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| KR20150077220A (en) * | 2013-12-27 | 2015-07-07 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| CN108391433A (en) * | 2015-12-04 | 2018-08-10 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and Organnic electroluminescent device comprising it |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20150077220A (en) * | 2013-12-27 | 2015-07-07 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
| CN108391433A (en) * | 2015-12-04 | 2018-08-10 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and Organnic electroluminescent device comprising it |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114437086A (en) * | 2022-02-24 | 2022-05-06 | 阜阳欣奕华材料科技有限公司 | Dicarbazole compound and preparation method and application thereof |
| CN115819427A (en) * | 2023-02-23 | 2023-03-21 | 夏禾科技(江苏)有限公司 | Synthetic method of benzo-quinoxaline-substituted indole and pyrrole fused azamacrocyclic compound |
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